Compound for organic electronic element, organic electronic element comprising the same and electronic device thereof

ABSTRACT

Provided are a compound of Formula 1 and an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device comprising the organic electric element, wherein the luminous efficiency and life span can be improved and the driving voltage of the organic electronic device can be lowered by comprising the compound represented by Formula 1 in the organic material layer.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims benefit under 119(a) (35 U.S.C. § 119(a))to Korean Patent Application No. 10-2014-0133993, filed on Oct. 06,2014, the contents of which are hereby incorporated by reference for allpurposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements comprising the same, and electronicdevices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electric element, andfor example, may include a hole injection layer, a hole transport layer,a light emitting layer, an electron transport layer, an electroninjection layer, or the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Currently, the power consumption is required more and more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is an important factor in the portabledisplay with a limited power source of the battery, and efficiency andlife span issue also must be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when an optimalcombination of energy levels and T1 values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.

Recently, in order to solve the problem of light emission in the holetransporting layer of an organic electric element, it is preferable thatan emission-auxiliary layer exists between the hole transport layer andthe light emitting layer. It is necessary to develop differentemission-auxiliary layer materials depending on the respective lightemitting layers (R, G, B).

In general, electrons are transferred from the electron transport layerto the light emitting layer and holes are transferred from the holetransport layer to the light emitting layer to generate excitons byrecombination.

However, since the material used for the hole transport layer has a lowHOMO value, it has a low T1 value, which causes the exciton generated inthe light emitting layer to be transferred to the hole transport layer.As a result, a charge unbalance occurs in the light emitting layer, andlight emission occurs in the hole transport layer or at the interface ofthe hole transport layer, resulting in showing poor color purity,reduced efficiency, and low life span.

In addition, when a material having a high hole mobility is used to makea low driving voltage, the efficiency tends to decrease. This is becausethe hole mobility is faster than the electron mobility in a generalorganic electronic element, resulting in a charge unbalance in the lightemitting layer. As a result, efficiency and life span are decreased.

Therefore, in order to solve the problems of the hole transport layerabove, an emission-auxiliary layer material should have a hole mobility(hole mobility: within driving voltage range of the full device bluedevice) and a high T₁ value (electron block) and a wide band gap.However, this cannot be achieved simply by the structural properties ofthe core of an emission-auxiliary layer material, but is possible whenthe combination of the core and sub-substituent properties of thematerial is combined. Accordingly, in order to improve the efficiencyand life span of the organic electronic device, it is strongly requiredto develop an emission-auxiliary layer material having a high T₁ valueand a wide band gap.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electronic device, a material forming the organicmaterial layer, for example, a hole injection material, a hole transportmaterial, a light emitting material, an electron transport material, anelectron injection material, an emission-auxiliary layer material or thelike, must be supported by a stable and efficient material. However,such a stable and efficient organic material layer material for anorganic electric element has not yet been fully developed. Accordingly,there is a continuous need to develop new materials for an organicmaterial layer, specifically, there are strong needs to developmaterials for an emission-auxiliary layer.

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention is to provide acompound capable of lowering the driving voltage of an organicelectronic element and improving the luminous efficiency, color purityand life span of the device, an organic electric element employing sucha compound, and an electronic device thereof.

In accordance with an aspect of the present invention, the compoundrepresented by the following Formula 1 is provided.

In another aspect of the present invention, organic electric elementscontaining the compound represented by the formula above and electronicdevices including the organic electric element are provided.

According to embodiment of the present invention, the driving voltage ofan organic electronic element can be lowered, and the luminousefficiency, color purity and life span of an organic electronic elementcan be improved.

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), chlorine (Cl), bromine (Br), iodine (I) and soon.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cyclo alkyl group (alicyclic), or an alkyl groupsubstituted with a cyclo alkyl.

Unless otherwise stated, the term “halo alkyl” or “halogen alkyl” asused herein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cyclo alkyl” as used herein means,but not limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxy group” or “alkyloxy group” as used herein means anoxygen radical attached to an alkyl group, but not limited to, and has 1to 60 carbon atoms.

The term “aryloxy group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means, univalent or bivalent functional groupwhich R, R′ and R″ are all hydrogen in the structural formula below.Also, “substituted fluorenyl group” or “substituted fluorenylene group”means, functional group which at least any one of R, R′ and R″ is afunctional group other than hydrogen and spiro compound which R and R′can be linked together with the carbon to which they are attached toform spiro compound.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group include a monocyclic rings, ring assemblies,fused polycyclic system or spiro compounds.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents at least one ofN, O, S, P and Si. The heterocyclic group means a monocyclic, ringassemblies, fused polycyclic system or spiro compound containing one ormore heteroatoms.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

In the present description, a monovalent or divalent functional groupmay be named as a functional group name or a parent compound name withvalence number in front of the parent compound name. For example,“divalent benzothiophene” means a divalent functional group ofbenzothiophene which is a parent compound, similarly, “divalentdibenzothiophene” means a divalent functional group of dibenzothiophenewhich is a parent compound, “divalent furan” means a divalent functionalgroup of furan which is a parent compound, “divalent dibenzofuran” meansa divalent functional group of dibenzofuran which is a parent compound,and “divalent pyridine” means a divalent functional group of a pyridinewhich is a parent compound. Likewise, a trivalent functional group canbe represented by a trivalent sign in front of the parent compound, forexample, “trivalent aryl” represents a trivalent functional group ofaryl which is aromatic, “trivalent fluorene” represents a trivalentfunctional group of fluorene.

Unless otherwise stated, the term “ring” as used herein comprisesmonocyclic and polycyclic rings, a heterocycle containing at least oneheteroatom as well as hydrocarbon ring, and both aromatic andnon-aromatic rings.

Unless otherwise stated, the term “polycyclic” as used herein means,ring assemblies like biphenyl and terphenyl, fused polycyclic system andspiro compound, an aromatic ring and a non-aromatic ring, and analiphatic ring and heterocyclic group containing at least oneheteroatom.

Unless otherwise stated, the term “ring assemblies” as used hereinmeans, two or more cyclic systems (single rings or fused systems) whichare directly joined to each other by double or single bonds are namedring assemblies when the number of such direct ring junctions is oneless than the number of cyclic systems involved. The ring assembliesalso mean, same or different ring systems are directly joined to eachother by double or single bonds.

Unless otherwise stated, the term “fused polycyclic system” as usedherein means, fused ring type which has at least two atoms as the commonmembers, fused two or more aliphatic ring systems and a fused heteroring system containing at least one heteroatom. Fused polycyclic systemis an aromatic ring, a hetero aromatic ring, an aliphatic ring, or thecombination of these.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro-’, ‘clispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an aryl alkoxymeans an alkoxy substituted with an aryl, an alkoxyl carbonyl means acarbonyl substituted with an alkoxyl, and an aryl carbonyl alkenyl alsomeans an alkenyl substitutes with an aryl carbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthiophene group, a C₆-C₂₀ arylthiophene group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₆₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R′s may be the same and different each other, and arelinked to the benzene ring as follows. when a is an integer of 4 to 6,the substituents R′s are linked to carbon atom of the benzene ring in asimilar manner to that. Meanwhile, hydrogen atoms linked to carbonconstituting the benzene ring may not be represented as usual.

FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer therebetween which contains the inventive compound. Here,the first electrode 120 may be an anode (positive electrode), and thesecond electrode 180 may be a cathode (negative electrode). In the caseof an inverted organic electric element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, at least one of the layers may not be formed.The organic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141 and so on, and the electron transport layer 160 and the like mayserve as the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an electron transport layer 160, an electron injection layer 170,as a host material or a dopant material of a light emitting layer 150,or as a material a capping layer material. For example, the inventivecompound may be used as material of the light emitting layer 150, thehole transport layer 140, and/or the emission-auxiliary layer 151.

On the other hand, even if the core is the same core, the band gap, theelectrical characteristics, the interface characteristics, and the likemay be different depending on which substituent is bonded at whichposition. Therefore, it is necessary to study the selection of the coreand the combination of the sub-substituent bonded to the core.Specially, long life span and high efficiency can be simultaneouslyachieved when the optimal combination of energy levels and T₁ values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers of an organic material layer isachieved.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, it ispreferable that an emission-auxiliary layer is formed between the holetransport layer and a light emitting layer, and it is time to developdifferent emission-auxiliary layers according to respective lightemitting layers (R, G, B). Meanwhile, even when a similar core is used,it is very difficult to infer the characteristics of anemission-auxiliary layer if a used organic material layer varies,because the correlation between the emission-auxiliary layer and a holetransport layer and between the emission-auxiliary layer and a lightemitting layer (host) must be figured out.

Accordingly, in the present invention, energy levels, T₁ values andinherent material properties (mobility, interfacial properties, etc.)among the respective organic material layers are optimized by forming ahole transport layer or/and an emission-auxiliary layer employingcompound represented by Formula 1, and thus the life span and efficiencyof the organic electric element can be improved at the same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate 110 toform the anode 120, forming the organic material layer including thehole injection layer 130, the hole transport layer 140, the lightemitting layer 150, the electron transport layer 160, and the electroninjection layer 170 thereon, and then depositing a material, which canbe used as the cathode 180, thereon. Also, an emission-auxiliary layer151 may be further formed between a hole transport layer 140 and a lightemitting layer 150.

Further, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transferprocess. Since the organic material layer according to the presentinvention may be formed in various ways, the scope of protection of thepresent invention is not limited by a method of forming the organicmaterial layer.

The organic electric element according to an embodiment of the presentinvention may be of a top emission type, a bottom emission type, or adual emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization, an excellent processability, and being producedby using conventional color filter technologies for LCDs. Variousstructures for WOLED which mainly used as back light units have beensuggested and patented. WOLED may employ various arrangement methods,representatively, a parallel side-by-side arrangement method of R(Red),G(Green), B(Blue) light-emitting units, a vertical stack arrangementmethod of RGB light-emitting units, and a CCM (color conversionmaterial) method in which electroluminescence from a blue (B) organiclight emitting layer, and the present invention may be applied to suchWOLED.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

The compound according to an aspect of the present invention isrepresented by the following Formula 1.

In the above formula, each symbol is defined as follows.

In formula 1, “A” and “B” may be each independently selected from thegroup consisting of formula 1-1, formula 1-2 and formula 1-3 below,wherein it is preferable that the case where “A” and “B” aresimultaneously the formula 1-3 is excluded. Also, it is preferable thatthe case where Ar¹ to Ar³ are all phenyl and L¹ is meta-phenylene when“A” is formula 1-1 is excluded.

In the above Formulas 1, 1-1 and 1-2, Ar¹ to Ar⁴ are each independentlyselected from the group consisting of a C₆-C₆₀ aryl group; a fluorenylgroup; a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si and P; a fused ringformed by a C₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring;—L′—N(R^(a)) (R^(b)); and the combination thereof, wherein Ar² and Ar³may be linked to each other to form a ring together with nitrogen towhich Ar² and Ar³ are bonded.

Preferably, Ar¹ to Ar⁴ may be each independently a C₆-C₂₅ aryl group, afluorenyl group, or a C₃-C₁₆ heterocyclic group, also preferably, a C₆,C₁₀, C₁₂, or C₁₄ aryl group, or a C₅, or C₁₂ heterocyclic group,specifically, a phenyl group, a naphthyl group, a biphenylyl group, aphenanthryl group, a fluorenyl group substituted or unsubstituted withmethyl or phenyl, a spirobifluorenyl group, a pyridyl group or adibenzothienyl group.

Preferably, Ar¹ to Ar⁴ may be further substituted with one or moresubstituents selected from the group consisting of deuterium; halogen; asilane group; a siloxane group; a boron group; a germanium group; acyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

In the above Formulas 1-1, 1-2 and 1-3, L¹ to L³ may be eachindependently selected from the group consisting of a single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a fused ring formed by aC₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring; a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P; and the combination thereof.

Preferably, the above L¹ to L³ may be each independently a single bond,a C₆-C₁₈ arylene group, a fluorenylene group, or a C₃-C₁₂ heterocyclicgroup and so on, also preferably, a C₆ arylene group, or a C₅ or C₁₂heterocyclic group, specifically, a single bond, a phenylene group, afluorenylene group substituted or unsubstituted with methyl or phenyl, aspirobifluorenylene group, a pyridylene group, a dibenzothienylenegroup, or a combination thereof.

Preferably, the above L¹ to L³ may be further substituted with one ormore substituents selected from the group consisting of deuterium;halogen; a silane group; a siloxane group; a boron group; a germaniumgroup; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

The above Formulas 1, 1-1, 1-2 and 1-3, R¹ to R¹⁶ may be eachindependently selected from the group consisting of hydrogen; deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si and P; a fused ring formed by a C₆-C₆₀aromatic ring and a C₃-C₆₀ aliphatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; —L′—N(R^(a))(R^(b)); and the combination thereof,wherein neighboring R¹s to R¹⁶s groups may be linked to each other toform a ring together with a benzene ring to which they are bonded.

Preferably, neighboring R¹s to R¹⁶s groups may be linked to each otherto form a ring together with a benzene ring to which they are bonded.For example, R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷and R⁸, R⁹ and R¹⁰, R¹⁰ and R¹¹, R¹¹ and R¹², R¹³ R and R¹⁴, R¹⁴ andR¹⁵, and/or R¹⁵ and R¹⁶ may be linked to each other to form a ringtogether with a benzene ring to which they are bonded. That is, at leasta couple of neighboring groups may be linked to each other to form aring. For example, R¹ and R² may be linked to each other to form a ringsuch as naphthalene together with the benzene ring to which they arebonded, and R³ to R¹⁶ may be also linked to each other to form a ring.

Preferably, R¹ to R¹⁶ not forming a ring may be each independentlyhydrogen or a C₆-C₁₈ aryl group, and also preferably also be a C₆ arylgroup, specifically hydrogen or a phenyl group.

Preferably, R¹ to R¹⁶ may be further substituted with one or moresubstituents selected from the group consisting of deuterium; halogen; asilane group; a siloxane group; a boron group; a germanium group; acyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

The above L′ may be selected from the group consisting of a single bond;a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring formed by aC₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring; and a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, and R^(a) and R^(b) may be eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a fused ring formed by a C₆-C₆₀ aromatic ring and aC₃-C₆₀ aliphatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P.

Specifically, the following Formulas 2 to 9 show the case where Formulas1-1, 1-2 and 1-3 are independently bonded to A and B of Formula 1.

In formulas 2 to 9, Ar¹ to Ar⁴, L¹ to L³, R¹ to R¹⁶, and the like arethe same as defined in Formulas 1, 1-1, 1-2 and 1-3 above.

More specifically, the compound represented by Formula 1 may be any oneof the following compounds.

In another aspect of the present invention, the present inventionprovides a compound represented by formula 1 for an organic electricelement.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising a compound representedby formula 1.

Here, an organic electric element may comprise a first electrode, asecond electrode, and an organic material layer formed between the firstelectrode and the second electrode, the organic material layer comprisesthe compound represented by Formula 1, and the compound may be comprisedin at least one layer of a hole injection layer, a hole transport layer,an emission-auxiliary layer and a light emitting layer. That is, thecompound represented by Formulas 1 may be used as material of a holeinjection layer, a hole transport layer, an emission-auxiliary layer ora light emitting layer. Preferably, the compound represented by Formula1 may be used as an emission-auxiliary layer material.

Preferably, there is provided an organic electric element comprising acompound represented by Formulas 2 to 9 in an organic electric element.

Preferably, there is provided an organic electric element comprising atleast one of compounds 1-1 to 1-28, 2-1 to 2-28, 3-1 to 3-28, 4-1 to4-16, 5-1 to 5-16, 6-1 to 6-12, 7-1 to 7-8, and 8-1 to 8-8 in an organicelectric element.

Preferably, the organic electric element may comprise the compoundrepresented by Formula 1 as a single compound or a mixture of two ormore kinds. For example, an emission-auxiliary layer of the organicmaterial layer may be formed of a single compound 1-1 or may be formedof a mixture of the compound 1-1 and the compound 1-2.

Meanwhile, the organic material layer may be formed by a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process, or a roll-to-roll process.

In another aspect of the present invention, the present inventionprovides an organic electric element further comprising at least a layerto improve luminous efficiency which is formed on at least one of thesides the first and second electrodes, which is opposite to the organicmaterial layer.

In another aspect of the present invention, the present inventionprovides an electronic device comprising a display device, wherein adisplay device comprises an organic electric element according to thepresent invention, and a control unit for controlling the displaydevice. Preferably, the organic electric element may be any one of anorganic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic orwhite illumination.

Hereinafter, Synthesis method of the compound represented by Formula 1according to one embodiment of the present invention and Preparationmethod of an organic electric element will be described in detail by wayof examples. However, the present invention is not limited to thefollowing examples.

SYNTHESIS EXAMPLE

The compound (final products) represented by Formula 1 according to thepresent invention are synthesized by reacting Sub 1 and Sub 2 as shownin Reaction Scheme 1, but are not limited thereto.

I. Synthesis Example of Sub 1

The compound Sub 1 of Reaction Scheme 1 is synthesized by the followingReaction Scheme 2, but is not limited thereto.

1. Synthesis Example of Sub 1-2

1) Synthesis of Sub 1-2(1) (“A” of formula 1 is formula 1-1 and L^(l) isa single bond)

Sub 1-1 (6.3 g, 20 mmol), Sub 1-1-1 (3.4 g, 20 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, followed by reaction at 100° C. Aftercompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated. The resulting compound was purified by silicagel columnand recrystallized to obtain 6.1 g (yield: 76%) of the product Sub1-2(1).

2) Synthesis of Sub 1-2(2) (“A” of formula 1 is formula 1-1 and L¹ isnot a single bond)

Sub 1-1 (5.0 g, 16 mmol), Sub 1-1-2 (6.7 g, 18 mmol), Pd(PPh₃)₄ (0.06 g,0.05 mmol) and K₂CO₃(6.6 g, 48 mmol) were dissolved in anhydrous THF anda small amount of water, and refluxed for 24 hours. When the reactionwas completed, the reactant was cooled to room temperature, extractedwith CH₂Cl₂ and washed with water. A small amount of water from thewashed product was removed with anhydrous MgSO₄. After filtration underreduced pressure, the organic solvent was concentrated, and theresulting product was separated by column chromatography to obtain 5.6 g(yield: 74%) of the product Sub 1-2(2).

3) Synthesis of Sub 1-2(3) (“A” of formula 1 is formula 1-2)

Sub 1-1 (5.0 g, 16 mmol), Sub 1-1-3 (8.0 g, 18 mmol), Pd(PPh₃)₄ (0.06 g,0.05 mmol) and K₂CO₃(6.6 g, 48 mmol) were dissolved in anhydrous THF anda small amount water, and 6.3 g (yield: 71%) of the product Sub 1-2(3)was obtained by using the same manner as described above for thesynthesis of compound Sub 1-2(2).

4) Synthesis of Sub 1-2(4) (“A” of formula 1 is formula 1 and L³ is asingle bond)

Sub 1-1 (6.3 g, 20 mmol), Sub 1-1-4 (3.3 g, 20 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene(300 mL) were added, and 6.0 g (yield: 75%) of the product Sub 1-2(4)was obtained by using the same manner as described above for thesynthesis of compound Sub 1-2(1).

5) Synthesis of Sub 1-2(5) (“A” of formula 1 is formula 1-3 and L³ isnot a single bond)

Sub 1-1 (5.0 g, 16 mmol), Sub 1-1-5 (6.6 g, 18 mmol), Pd(PPb₃)₄ (0.06 g,0.05 mmol), K₂CO₃(6.6 g, 48 mmol) were dissolved in anhydrous THF and asmall amount water, and 5.5 g (yield: 72%) of the product Sub 1-2(5) wasobtained by using the same manner as described above for the synthesisof compound Sub 1-2(2).

2. Synthesis Example of Sub 1-3

Sub 1-3 can be synthesized by using the synthesis methods of Sub 1-2(1)and Sub 1-2(2) when “B” in formula 1 is the formula 1-1, by using thesynthesis method of Sub 1-2(3) when “B” in formula 1 is the formula 1-2,and by using the synthesis methods of Sub 1-2(4) and Sub 1-2(5) when “B”in formula 1 is the formula 1-3.

Meanwhile, examples of Sub 1-3 are as followings, but are not limitedto, and Table 1 below shows the FD-MS values thereof.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-3(1) m/z = 490.10(C₃₀H₂₃BrN₂= 491.42) Sub 1-3(2) m/z = 642.17(C₄₂H₃₁BrN₂ = 643.61) Sub 1-3(3) m/z =492.09(C₂₈H₂₁BrN₄ = 493.40) Sub 1-3(4) m/z = 566.14(C₃₆H₂₇BrN₂ = 567.52)Sub 1-3(5) m/z = 642.17(C₄₂H₃₁BrN₂ = 643.61) Sub 1-3(6) m/z =742.20(C₅₀H₃₅BrN₂ = 743.73) Sub 1-3(7) m/z = 742.20(C₅₀H₃₅BrN₂ = 743.73)Sub 1-3(8) m/z = 946.29(C₆₆H₄₇BrN₂ = 948.00) Sub 1-3(9) m/z =564.12(C₃₆H₂₅BrN₂ = 565.50) Sub 1-3(10) m/z = 640.15(C₄₂H₂₉BrN₂ =641.60) Sub 1-3(11) m/z = 565.12(C₃₅H₂₄BrN₃ = 566.49) Sub 1-3(12) m/z =670.11(C₄₂H₂₇BrN₂S = 671.65) Sub 1-3(13) m/z = 640.15(C₄₂H₂₉BrN₂ =641.60) Sub 1-3(14) m/z = 740.18(C₅₉H₃₃BrN₂ = 741.71) Sub 1-3(15) m/z =740.18(C₅₀H₃₃BrN₂ = 741.71) Sub 1-3(16) m/z = 944.28(C₆₆H₄₅BrN₂ =945.98) Sub 1-3(17) m/z = 538.10(C₃₄H₂₃BrN₂ = 539.46) Sub 1-3(18) m/z =640.15(C₄₂H₂₉BrN₂ = 641.60) Sub 1-3(19) m/z = 489.08(C₂₉H₂₀BrN₃ =490.39) Sub 1-3(20) m/z = 564.12(C₃₆H₂₅BrN₂ = 565.50) Sub 1-3(21) m/z =640.15(C₄₂H₂₉BrN₂ = 641.60) Sub 1-3(22) m/z = 690.17(C₄₆H₃₁BrN₂ =691.66) Sub 1-3(23) m/z = 740.18(C₅₀H₃₃BrN₂ = 741.71) Sub 1-3(24) m/z =944.28(C₆₆H₄₅BrN₂ = 945.98) Sub 1-3(25) m/z = 639.13(C₄₁H₂₆BrN₃ =640.57) Sub 1-3(26) m/z = 638.14(C₄₂H₂₇BrN₂ = 639.58) Sub 1-3(27) m/z =640.13(C₄₀H₂₅BrN₄ = 641.56) Sub 1-3(28) m/z = 744.12(C₄₈H₂₉BrN₂S =745.73) Sub 1-3(29) m/z = 790.20(C₅₄H₃₅BrN₂ = 791.77) Sub 1-3(30) m/z =790.20(C₅₄H₃₅BrN₂ = 791.77) Sub 1-3(31) m/z = 714.17(C₄₈H₃₁BrN₂ =715.68) Sub 1-3(32) m/z = 792.19(C₅₂H₃₃BrN₄ = 793.75) Sub 1-3(33) m/z =638.14(C₄₂H₂₇BrN₂ = 639.58) Sub 1-3(34) m/z = 638.14(C₄₂H₂₇BrN₂ =639.58) Sub 1-3(35) m/z = 714.17(C₄₈H₃₁BrN₂ = 715.68) Sub 1-3(36) m/z =714.17(C₄₈H₃₁BrN₂ = 715.68) Sub 1-3(37) m/z = 792.19(C₅₂H₃₃BrN₄ =793.75) Sub 1-3(38) m/z = 870.17(C₅₈H₃₅BrN₂S = 871.88) Sub 1-3(39) m/z =764.18(C₅₂H₃₃BrN₂ = 765.74) Sub 1-3(40) m/z = 714.17(C₄₈H₃₁BrN₂ =715.68)

3. Synthesis Example of Sub 1-5

Sub 1-3(1) (7.9 g, 16 mmol), Sub 1-4(1) (5.5 g, 18 mmol), Pd(PPh₃)₄(0.06 g, 0.05 mmol) and K₂CO₃(6.6 g, 48 mmol) were dissolved inanhydrous THF and a small amount water, and 3.9 g (yield: 76%) of theproduct Sub 1-5(1) was obtained by using the same manner as describedabove for the synthesis of compound Sub 1-2(2).

4. Synthesis Example of Sub 1

Sub 1-5(1) (6.4g, 12mmol) and triphenylphosphine were dissolved ino-dichlorobenzene and refluxed for 24 hours. When the reaction wascompleted, the solvent was removed by distillation under reducedpressure, and the concentrated product was separated by columnchromatography to obtain 4.7 g (yield: 78%) of the product Sub 1 (1).

Meanwhile, examples of Sub 1 are as followings, but are not limited to,and Table 2 below shows the FD-MS values thereof.

TABLE 2 compound FD-MS compound FD-MS Sub 1(1) m/z = 501.22(C₃₀H₂₇N₃ =501.62) Sub 1(2) m/z = 653.28(C₄₈H₃₅N₃ = 653.81) Sub 1(3) m/z =503.21(C₃₄H₂₈N₃ = 503.60) Sub 1(4) m/z = 577.25(C₄₂H₃₁N₃ = 577.72) Sub1(5) m/z = 653.28(C₄₈H₃₅N₃ = 653.81) Sub 1(6) m/z = 753.31(C₅₆H₃₉N₃ =753.93) Sub 1(7) m/z = 753.31(C₅₆H₁₉N₃ = 753.93) Sub 1(8) m/z =957.41(C₇₂H₅₁N₃ = 958.20) Sub 1(9) m/z = 575.24(C₄₂H₂₉N₃ = 575.70) Sub1(10) m/z = 651.27(C₄₈H₃₃N₃ = 651.80) Sub 1(11) m/z = 576.23(C₄₁H₂₈N₄ =576.69) Sub 1(12) m/z = 681.22(C₄₈H₃₁N₃S = 681.84) Sub 1(13) m/z =651.27(C₄₈H₃₃N₃ = 651.80) Sub 1(14) m/z = 751.30(C₅₆H₃₇N₃ = 751.91) Sub1(15) m/z = 751.30(C₅₆H₃₇N₃ = 751.91) Sub 1(16) m/z = 955.39(C₇₂H₄₉N₃ =956.18) Sub 1(17) m/z = 549.22(C₄₀H₃₇N₃ = 549.66) Sub 1(18) m/z =651.27(C₄₈H₃₃N₃ = 651.80) Sub 1(19) m/z = 500.20(C₃₅H₂₄N₄ = 500.59) Sub1(20) m/z = 575.24(C₄₂H₂₉N₃ = 575.70) Sub 1(21) m/z = 651.27(C₃₈H₃₃N₃ =651.80) Sub 1(22) m/z = 701.28(C₅₂H₃₅N₃ = 701.85) Sub 1(23) m/z =751.30(C₅₀H₃₇N₃ = 751.91) Sub 1(24) m/z = 955.39(C₇₂H₄₈N₃ = 956.18) Sub1(25) m/z = 650.25(C₄₇H₃₀N₄ = 650.77) Sub 1(26) m/z = 649.25(C₄₈H₃₁N₃ =649.78) Sub 1(27) m/z = 651.24(C₄₆H₂₉N₃ = 651.76) Sub 1(28) m/z =755.24(C₅₄H₃₃NS = 755.92) Sub 1(29) m/z = 801.31(C₃₀H₂₉N₃ = 801.967) Sub1(30) m/z = 801.31(C₃₀H₃₉N₃ = 801.97) Sub 1(31) m/z = 825.28(C₃₄H₃₅N₃ =725.88) Sub 1(32) m/z = 803.30(C₅₈H₂₇N₃ = 803.95) Sub 1(33) m/z =649.25(C₄₈H₃₅N₃ = 649.78) Sub 1(34) m/z = 649.25(C₄₈H₃₁N₃ = 649.78) Sub1(35) m/z = 725.28(C₅₄H₃₅N₃ = 725.88) Sub 1(36) m/z = 725.28(C₅₄H₃₅N₃ =725.88) Sub 1(37) m/z = 803.30(C₅₈H₃₇N₃ = 803.95) Sub 1(38) m/z =881.29(C₄₄H₂₉N₃S = 882.08) Sub 1(39) m/z = 775.30(C₅₈H₃₇N₃ = 775.93) Sub1(40) m/z = 725.28(C₅₄H₃₅N₃ = 725.88) Sub 1(41) m/z = 691.30(C₅₁H₃₇N₃ =691.86) Sub 1(42) m/z = 699.27(C₅₂H₃₃N₃ = 699.84) Sub 1(43) m/z =574.22(C₄₁H₂₆N₄ = 574.67) Sub 1(44) m/z = 575.24(C₃₂H₂₉N₃ = 575.70) Sub1(45) m/z = 573.22(C₄₂H₂₉N₃ = 573.68)

I. Example of Sub 2

Examples of Sub 2 of the reaction scheme 1 are as followings, but arenot limited to.

III. Synthesis Example of Final Products 1. Synthesis Example ofCompound 1-1

Sub 1(1) (10.0 g, 20 mmol), Sub 2-1 (3.5 g, 22 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300mL) were added, followed by reaction at 100° C. Aftercompletion of the reaction, the reaction product was extracted withCH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated. The resulting compound was purified by silicagel columnand recrystallized to obtain 6.5 g (yield: 65%) of the product 1-1.

2. Synthesis example of compound 2-5

Sub 1(41) (13.8 g, 20 mmol), Sub 2-1 (3.5 g, 22 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 9.5 g (yield: 62%) of the product 2-5was obtained by using the same manner as described above for thesynthesis of the product 1-1.

3. Synthesis Example of Compound 3-9

Sub 1(17) (11.0 g, 20 mmol), Sub 2-16 (5.8 g, 22 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 8.8 g (yield: 60%) of the product 3-9was obtained by using the same manner as described above for thesynthesis of the product 1-1.

4. Synthesis Example of Compound 4-13

Sub 1(42) (14.0 g, 20 mmol), Sub 2-1 (3.5 g, 22 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 9.8 g (yield: 63%) of the product 4-13was obtained by using the same manner as described above for thesynthesis of the product 1-1.

5. Synthesis Example of Compound 5-5

Sub 1(43) (14.0 g, 20 mmol), Sub 2(1) (3.5 g, 22 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 8.5 g (yield: 65%) of the product 5-5was obtained by using the same manner as described above for thesynthesis of the product 1-1.

6. Synthesis Example of Compound 6-9

Sub 1(44) (11.5 g, 20 mmol), Sub 2-10- (5.8 g, 22 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 8.9 g (yield: 59%) of the product 6-9was obtained by using the same manner as described above for thesynthesis of the product 1-1.

7. Synthesis example of compound 7-7

Sub 1(23) (15.0 g, 20 mmol), Sub 2-1 (3.5 g, 22 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 10.8 g (yield: 65%) of the product 7-7was obtained by using the same manner as described above for thesynthesis of the product 1-1.

8. Synthesis example of compound 8-4

Sub 1(45) (11.5 g, 20 mmol), Sub 2-17 (6.0 g, 22 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were added, and 9.2 g (yield: 60%) of the product 8-4was obtained by using the same manner as described above for thesynthesis of the product 1-1.

Meanwhile, Table 3 shows FD-MS values of the compounds of the presentinvention prepared according to the above synthesis example.

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 577.25(C₄₂H₃₁N₃ =577.72) 1-2 m/z = 677.28(C₅₀H₃₅N₃ = 677.83) 1-3 m/z = 677.28(C₅₀H₃₅N₃ =677.83) 1-4 m/z = 881.38(C₆₆H₄₇N₃ = 882.10) 1-5 m/z = 809.38(C₆₀H₄₇N₃ =810.04) 1-6 m/z = 1057.44(C₈₀H₅₅N₃ = 1058.31) 1-7 m/z = 1053.41(C₈₀H₅₁N₃= 1054.28) 1-8 m/z = 789.23(C₅₄H₃₅N₃S₂ = 790.01) 1-9 m/z =683.24(C₄₈H₃₃N₃S = 683.86) 1-10 m/z = 730.31(C₅₃H₃₈N₄ = 730.90) 1-11 m/z= 579.24(C₄₀H₂₉N₅ = 579.69) 1-12 m/z = 653.28(C₄₈H₃₅N₃ = 653.81) 1-13m/z = 729.31(C₅₄H₃₉N₃ = 729.91) 1-14 m/z = 829.35(C₆₂H₄₃N₃ = 830.02)1-15 m/z = 829.35(C₆₂H₄₃N₃ = 830.02) 1-16 m/z = 1033.44(C₇₈H₅₅N₃ =1034.29) 1-17 m/z = 961.44(C₇₂H₅₅N₃ = 962.23) 1-18 m/z =1209.50(C₉₂H₆₃N₃ = 1210.50) 1-19 m/z = 1205.47(C₉₂H₅₉N₃ = 1206.47) 1-20m/z = 941.29(C₆₆H₄₃N₃S₂ = 942.20) 1-21 m/z = 835.30(C₆₀H₄₁N₃S = 836.05)1-22 m/z = 882.37(C₆₅H₄₆N₄ = 883.09) 1-23 m/z = 731.30(C₅₂H₃₇N₅ =731.88) 1-24 m/z = 807.34(C₅₈H₄₁N₅ = 807.98) 1-25 m/z =941.29(C₆₆H₄₃N₃S₂ = 942.20) 1-26 m/z = 961.44(C₇₂H₅₅N₃ = 962.23) 1-27m/z = 1209.50(C₉₂H₆₃N₃ = 1210.50) 1-28 m/z = 1209.50(C₉₂H₆₃N₃ = 1210.50)2-1 m/z = 651.27(C₄₈H₃₃N₃ = 651.80) 2-2 m/z = 701.28(C₅₂H₃₅N₃ = 701.85)2-3 m/z = 701.28(C₅₂H₃₅N₃ = 701.85) 2-4 m/z = 803.33(C₆₀H₄₁N₃ = 803.99)2-5 m/z = 767.33(C₅₇H₄₁N₃ = 767.96) 2-6 m/z = 891.36(C₆₇H₄₅N₃ = 892.09)2-7 m/z = 889.35(C₆₇H₄₃N₃ = 890.08) 2-8 m/z = 857.29(C₆₂H₃₉N₃S = 858.06)2-9 m/z = 757.26(C₅₄H₃₅N₃S = 757.94) 2-10 m/z = 728.29(C₅₃H₃₆N₄ =728.88) 2-11 m/z = 652.26(C₄₇H₃₂N₄ = 652.78) 2-12 m/z = 757.26(C54H35N3S= 757.94) 2-13 m/z = 727.30(C₅₄H₃₇N₃ = 727.89) 2-14 m/z =827.33(C₆₂H₄₁N₃ = 828.01) 2-15 m/z = 827.33(C₆₂H₄₁N₃ = 828.01) 2-16 m/z= 1031.42(C₇₈H₅₃N₃ = 1032.28) 2-17 m/z = 843.36(C₆₃H₄₅N₃ = 844.05) 2-18m/z = 967.39(C₇₃H₄₉N₃ = 968.19) 2-19 m/z = 965.38(C₇₃H₄₇N₃ = 966.17)2-20 m/z = 833.29(C₆₀H₃₉N₃S = 834.04) 2-21 m/z = 833.29(C₆₀H₃₉N₃S =834.04) 2-22 m/z = 880.36(C₆₅H₄₄N₄ = 881.07) 2-23 m/z = 728.29(C₅₃H₃₆N₄= 728.88) 2-24 m/z = 803.33(C₆₀H₄₁N₃ = 803.99) 2-25 m/z =1015.31(C₇₂H₄₅N₃S₂ = 1016.28) 2-26 m/z = 803.33(C₆₀H₄₁N₃ = 803.99) 2-27m/z = 1283.52(C₉₈H₆₅N₃ = 1284.58) 2-28 m/z = 1279.49(C₉₈H₆₁N₃ = 1280.55)3-1 m/z = 575.24(C₄₂H₂₉N₃ = 575.70) 3-2 m/z = 625.25(C₄₆H₃₁N₃ = 625.76)3-3 m/z = 625.25(C₄₆H₃₁N₃ = 625.76) 3-4 m/z = 727.30(C₅₄H₃₇N₃ = 727.89)3-5 m/z = 691.30(C₅₁H₃₇N₃ = 691.86) 3-6 m/z = 815.33(C₆₁H₄₁N₃ = 816.00)3-7 m/z = 813.31(C₆₁H₃₉N₃ = 813.98) 3-8 m/z = 681.22(C₄₈H₃₁N₃S = 681.84)3-9 m/z = 731.24(C₅₂H₃₃N₃S = 731.90) 3-10 m/z = 728.29(C₅₃H₃₆N₄ =728.88) 3-11 m/z = 576.23(C₄₁H₂₈N₄ = 576.69) 3-12 m/z = 651.27(C₄₈H₃₃N₃= 651.80) 3-13 m/z = 727.30(C₅₄H₃₇N₃ = 727.89) 3-14 m/z =777.31(C₅₈H₃₉N₃ = 777.95) 3-15 m/z = 827.33(C₆₂H₄₁N₃ = 828.01) 3-16 m/z= 1031.42(C₇₈H₅₃N₃ = 1032.28) 3-17 m/z = 843.36(C₆₃H₄₅N₃ = 844.05) 3-18m/z = 967.39(C₇₃H₄₉N₃ = 968.19) 3-19 m/z = 965.38(C₇₃H₄₇N₃ = 966.17)3-20 m/z = 833.29(C₆₀H₃₉N₃S = 834.04) 3-21 m/z = 833.29(C₆₀H₃₉N₃S =834.04) 3-22 m/z = 880.36(C₆₅H₄₄N₄ = 881.07) 3-23 m/z = 728.29(C₅₃H₃₆N₄= 728.88) 3-24 m/z = 805.32(C₅₈H₃₉N₅ = 805.96) 3-25 m/z =939.27(C₆₆H₄₁N₃S₂ = 940.18) 3-26 m/z = 959.42(C₇₂H₅₃N₃ = 960.21) 3-27m/z = 1207.49(C₉₂H₆₁N₃ = 1208.49) 3-28 m/z = 1207.49(C₉₂H₆₁N₃ = 1208.49)4-1 m/z = 725.28(C₅₄H₃₅N₃ = 725.88) 4-2 m/z = 775.30(C₅₈H₃₇N₃ = 775.93)4-3 m/z = 775.30(C₅₈H₃₇N₃ = 775.93) 4-4 m/z = 801.31(C₆₀H₃₉N₃ = 801.97)4-5 m/z = 726.28(C₅₃H₃₄N₄ = 726.86) 4-6 m/z = 726.28(C₅₃H₃₄N₄ = 726.86)4-7 m/z = 726.28(C₅₃H₃₄N₄ = 726.86) 4-8 m/z = 831.27(C₆₀H₃₇N₃S = 832.02)4-9 m/z = 977.38(C₇₄H₄₇N₃ = 978.19) 4-10 m/z = 877.35(C₆₆H₄₃N₃ = 878.07)4-11 m/z = 801.31(C₆₀H₃₉N₃ = 801.97) 4-12 m/z = 879.34(C₆₄H₄₁N₅ =880.04) 4-13 m/z = 775.30(C₅₈H₃₇N₃ = 775.93) 4-14 m/z = 825.31(C₆₂H₃₉N₃= 825.99) 4-15 m/z = 825.31(C₆₂H₃₉N₃ = 825.99) 4-16 m/z =953.38(C₇₂H₄₇N₃ = 954.16) 5-1 m/z = 649.25(C₄₈H₃₁N₃ = 649.78) 5-2 m/z =699.27(C₅₂H₃₃N₃ = 699.84) 5-3 m/z = 699.27(C₅₂H₃₃N₃ = 699.84) 5-4 m/z =725.28(C₅₄H₃₅N₃ = 725.88) 5-5 m/z = 650.25(C₄₇H₃₀N₄ = 650.77) 5-6 m/z =650.25(C₄₇H₃₀N₄ = 650.77) 5-7 m/z = 861.23(C₆₀H₃₅N₃S₂ = 862.07) 5-8 m/z= 765.31(C₅₇H₃₉N₃ = 765.94) 5-9 m/z = 725.28(C₅₄H₃₅N₃ = 725.88) 5-10 m/z= 725.28(C₅₄H₃₅N₃ = 725.88) 5-11 m/z = 801.31(C₆₀H₃₉N₃ = 801.97) 5-12m/z = 801.31(C₆₀H₃₉N₃ = 801.97) 5-13 m/z = 879.34(C₆₄H₄₁N₅ = 880.04)5-14 m/z = 957.32(C₇₀H₄₃N₃S = 958.18) 5-15 m/z = 851.33(C₆₄H₄₁N₃ =852.03) 5-16 m/z = 851.33(C₆₄H₄₁N₃ = 852.03) 6-1 m/z = 651.27(C₄₈H₃₃N₃ =651.80) 6-2 m/z = 701.28(C₅₂H₃₅N₃ = 701.85) 6-3 m/z = 701.28(C₅₂H₃₅N₃ =701.85) 6-4 m/z = 803.33(C₆₀H₄₁N₃ = 803.99) 6-5 m/z = 767.33(C₅₇H₄₁N₃ =767.96) 6-6 m/z = 891.36(C₆₇H₄₅N₃ = 892.09) 6-7 m/z = 889.35(C₆₇H₄₃N₃ =890.08) 6-8 m/z = 857.29(C₆₂H₃₉N₃S = 858.06) 6-9 m/z = 757.26(C₅₄H₃₅N₃S= 757.94) 6-10 m/z = 728.29(C₅₃H₃₆N₄ = 728.88) 6-11 m/z =652.26(C₄₇H₃₂N₄ = 652.78) 6-12 m/z = 757.26(C54H35N3S = 757.94) 7-1 m/z= 731.24(C₅₂H₃₃N₃S = 731.90) 7-2 m/z = 728.29(C₅₃H₃₆N₄ = 728.88) 7-3 m/z= 576.23(C₄₁H₂₈N₄ = 576.69) 7-4 m/z = 651.27(C₄₈H₃₃N₃ = 651.80) 7-5 m/z= 727.30(C₅₄H₃₇N₃ = 727.89) 7-6 m/z = 777.31(C₅₈H₃₉N₃ = 777.95) 7-7 m/z= 827.33(C₆₂H₄₁N₃ = 828.01) 7-8 m/z = 1031.42(C₇₈H₅₃N₃ = 1032.28) 8-1m/z = 650.25(C₄₇H₃₀N₄ = 650.77) 8-2 m/z = 650.25(C₄₇H₃₀N₄ = 650.77) 8-3m/z = 861.23(C₆₀H₃₅N₃S₂ = 862.07) 8-4 m/z = 765.31(C₅₇H₃₉N₃ = 765.94)8-5 m/z = 725.28(C₅₄H₃₅N₃ = 725.88) 8-6 m/z = 725.28(C₅₄H₃₅N₃ = 725.88)8-7 m/z = 801.31(C₆₀H₃₉N₃ = 801.97) 8-8 m/z = 801.31(C₆₀H₃₉N₃ = 801.97)

Fabrication and Evaluation of Organic Electronic Element [Example 1]Green OLED(An Emission-Auxiliary Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material.

First, an ITO layer (anode) was formed on a glass substrate, and then4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,“2-TNATA”) was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm.

Subsequently,N,N′-Bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter, “NPB”) was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer.

Subsequently, compound 1-1 of the present invention was vacuum-depositedon the hole transport layer to form a emission-auxiliary layer with athickness of 20 nm.

A light emitting layer with a thickness of 30 nm was deposited on theemission-auxiliary layer by using 4,4′-N,N′-dicarbazole-biphenyl(hereinafter, “CBP”) as a host material andtris(2-phenylpyridine)-iridium (hereinafter, “Ir(ppy)₃”) as a dopantmaterial in a weight ratio of 95:5.

Next, (1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, andtris-(8-hydroxyquinoline)aluminum (hereinafter, “Alq₃”) wasvacuum-deposited with a thickness of 40 nm to form an electron transportlayer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example 2] to [Example 28] Green OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in Example 1except that any one of the inventive compounds described in Table 4instead of the inventive compound 1-1 was used as an emission-auxiliarylayer material.

[Comparative Example 1]

The OLED was fabricated in the same manner as described in Example 1except that an emission-auxiliary layer was not formed.

[Comparative Example 2] to [Comparative Example 9]

The OLEDs were fabricated in the same manner as described in Example 1except that any one of Comparative compounds 1 to instead of theinventive compound 1-1 was used as an emission-auxiliary layer material.

Electroluminescence (EL) characteristics were measured with aPR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 1 to 28 of the present invention and ComparativeExamples 1 to 9. And, the T95 life span was measured using a life spanmeasuring apparatus manufactured by Macscience Inc. at referencebrightness of 5000 cd/m². The measurement results are shown in Table 4below.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIE EALcom. (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(1) — 5.9 14.0 5000.035.6 77.1 0.33 0.61 comp. Ex(2) comp. Com1 6.2 12.4 5000.0 40.2 111.60.33 0.61 comp. Ex(3) comp. Com2 6.1 11.9 5000.0 41.9 102.2 0.33 0.61comp. Ex(4) comp. Com3 6.1 12.1 5000.0 41.3 111.9 0.33 0.61 comp. Ex(5)comp. Com4 6.3 10.6 5000.0 47.2 102.4 0.33 0.61 comp. Ex(6) comp. Com56.1 10.6 5000.0 47.2 107.6 0.33 0.62 comp. Ex(7) comp. Com6 6.0 11.15000.0 45.0 118.3 0.33 0.61 comp. Ex(8) comp. Com7 6.3 11.4 5000.0 43.9110.9 0.33 0.61 comp. Ex(9) comp. Com8 6.2 10.2 5000.0 49.2 119.3 0.330.62 Ex. (1) 1-1 6.1 9.2 5000.0 54.5 123.9 0.33 0.62 Ex. (2) 1-8 5.9 9.45000.0 53.1 123.5 0.33 0.62 Ex. (3) 1-9 6.0 9.2 5000.0 54.5 132.9 0.330.61 Ex. (4) 1-12 6.0 9.4 5000.0 53.5 135.9 0.33 0.61 Ex. (5) 1-13 6.29.2 5000.0 54.1 125.1 0.33 0.62 Ex. (6) 2-1 6.1 9.0 5000.0 55.8 128.60.33 0.61 Ex. (7) 2-7 6.2 8.8 5000.0 56.9 140.8 0.33 0.62 Ex. (8) 2-106.1 8.8 5000.0 56.7 130.3 0.33 0.62 Ex. (9) 2-14 5.9 8.9 5000.0 56.4140.8 0.33 0.62 Ex. (10) 2-23 6.0 8.9 5000.0 56.3 131.8 0.33 0.61 Ex.(11) 3-4 6.1 8.8 5000.0 56.7 146.7 0.33 0.62 Ex. (12) 3-8 6.1 8.9 5000.056.3 125.8 0.33 0.61 Ex. (13) 3-10 6.3 8.9 5000.0 56.4 124.2 0.33 0.62Ex. (14) 3-13 6.0 9.0 5000.0 55.8 131.1 0.33 0.61 Ex. (15) 3-25 6.0 8.95000.0 56.1 144.2 0.33 0.61 Ex. (16) 4-1 5.9 7.9 5000.0 63.6 142.8 0.330.62 Ex. (17) 4-6 6.1 7.7 5000.0 65.0 147.5 0.33 0.61 Ex. (18) 4-11 6.27.8 5000.0 64.1 140.8 0.33 0.61 Ex. (19) 5-4 6.0 8.0 5000.0 62.3 148.70.33 0.62 Ex. (20) 5-12 6.2 8.0 5000.0 62.7 124.2 0.33 0.61 Ex. (21)5-16 6.2 8.0 5000.0 62.6 124.6 0.33 0.61 Ex. (22) 6-1 6.3 8.1 5000.061.7 149.5 0.33 0.62 Ex. (23) 6-7 6.3 8.1 5000.0 61.8 148.1 0.33 0.61Ex. (24) 6-12 6.1 8.1 5000.0 61.5 129.8 0.33 0.62 Ex. (25) 7-3 6.0 8.75000.0 57.4 135.1 0.33 0.62 Ex. (26) 7-5 6.1 8.6 5000.0 58.3 147.5 0.330.61 Ex. (27) 8-5 6.2 8.4 5000.0 59.3 128.9 0.33 0.61 Ex. (28) 8-8 5.98.8 5000.0 57.1 145.7 0.33 0.61

[Example 29] Red OLED (An Emission-Auxiliary Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material.

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, NPB wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer.

Subsequently, the compound 1-2 of the present invention wasvacuum-deposited on the hole transport layer to form aemission-auxiliary layer with a thickness of 20 nm.

A light emitting layer with a thickness of 30 nm was deposited on theemission-auxiliary layer by using the CBP as a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (“(piq)₂Ir(acac)”)as a dopant material in a weight ratio of 95:5.

Next, BAlq was vacuum-deposited with a thickness of 10 nm on the lightemitting layer to form a hole blocking layer, Alq₃ was vacuum-depositedwith a thickness of 40 nm to form an electron transport layer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example 30] to [Example 56] Red OLED (An Emission-Auxiliary Layer)

The OLEDs were fabricated in the same manner as described in Example 29except that any one of the inventive compounds described in Table 5instead of the inventive compound 1-2 was used as an emission-auxiliarylayer material.

[Comparative Example 10]

The OLED was fabricated in the same manner as described in Example 29except that an emission-auxiliary layer was not formed.

[Comparative Example 11] to [Comparative Example 18]

The OLEDs were fabricated in the same manner as described in Example 29except that any one of Comparative compounds 1 to 8 above instead of theinventive compound 1-2 was used as an emission-auxiliary layer material.

Electroluminescence (EL) characteristics were measured with aPR-650(Photoresearch) by applying a forward bias DC voltage to the OLEDsprepared in Examples 29 to 59 of the present invention and ComparativeExamples 10 to 18. And, the T95 life span was measured using a life spanmeasuring apparatus manufactured by Macscience Inc. at referencebrightness of 2500 cd/m². The measurement results are shown in Table 5below.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime CIE EALcom. (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(10) — 6.2 32.92500.0 7.6 84.9 0.66 0.34 comp. Ex(11) comp. Com1 6.3 30.7 2500.0 8.2105.1 0.65 0.34 comp. Ex(12) comp. Com2 6.3 30.4 2500.0 8.2 101.7 0.660.32 comp. Ex(13) comp. Com3 6.3 30.3 2500.0 8.3 116.0 0.67 0.34 comp.Ex(14) comp. Com4 6.3 30.7 2500.0 8.2 105.8 0.66 0.33 comp. Ex(15) comp.Com5 6.2 26.8 2500.0 9.3 116.7 0.66 0.33 comp. Ex(16) comp. Com6 6.326.8 2500.0 9.3 110.4 0.66 0.33 comp. Ex(17) comp. Com7 6.4 28.5 2500.08.8 115.7 0.66 0.32 comp. Ex(18) comp. Com8 6.3 25.3 2500.0 9.9 118.70.66 0.33 Ex. (29) 1-2 6.2 18.4 2500.0 13.6 123.9 0.67 0.33 Ex. (30)1-10 6.2 18.9 2500.0 13.2 123.5 0.66 0.34 Ex. (31) 1-11 6.2 18.9 2500.013.2 132.9 0.67 0.34 Ex. (32) 1-14 6.3 18.1 2500.0 13.8 135.9 0.66 0.33Ex. (33) 1-17 6.2 18.4 2500.0 13.6 125.1 0.66 0.32 Ex. (34) 2-2 6.4 16.42500.0 15.3 128.6 0.67 0.34 Ex. (35) 2-8 6.3 16.4 2500.0 15.2 140.8 0.650.33 Ex. (36) 2-11 6.3 16.5 2500.0 15.1 130.3 0.66 0.34 Ex. (37) 2-156.3 16.0 2500.0 15.6 140.8 0.67 0.33 Ex. (38) 2-24 6.3 16.6 2500.0 15.0131.8 0.67 0.34 Ex. (39) 3-5 6.4 16.3 2500.0 15.4 146.7 0.67 0.33 Ex.(40) 3-9 6.3 16.0 2500.0 15.6 125.8 0.67 0.32 Ex. (41) 3-11 6.2 16.12500.0 15.5 124.2 0.66 0.33 Ex. (42) 3-14 6.3 16.3 2500.0 15.3 131.10.67 0.33 Ex. (43) 3-26 6.3 16.8 2500.0 14.9 144.2 0.66 0.34 Ex. (44)4-2 6.4 12.2 2500.0 20.5 142.8 0.66 0.33 Ex. (45) 4-5 6.3 12.3 2500.020.3 147.5 0.66 0.33 Ex. (46) 4-10 6.3 12.1 2500.0 20.7 140.8 0.65 0.32Ex. (47) 5-5 6.2 13.3 2500.0 18.8 148.7 0.65 0.34 Ex. (48) 5-13 6.3 13.22500.0 19.0 124.2 0.66 0.32 Ex. (49) 5-17 6.4 13.6 2500.0 18.3 124.60.66 0.33 Ex. (50) 6-3 6.4 13.3 2500.0 18.8 149.5 0.66 0.32 Ex. (51) 6-86.3 13.7 2500.0 18.2 148.1 0.66 0.34 Ex. (52) 6-15 6.2 13.7 2500.0 18.2129.8 0.66 0.33 Ex. (53) 7-4 6.2 15.3 2500.0 16.3 135.1 0.65 0.32 Ex.(54) 7-6 6.3 14.2 2500.0 17.6 147.5 0.67 0.34 Ex. (55) 8-3 6.3 14.92500.0 16.8 128.9 0.65 0.33 Ex. (56) 8-10 6.2 14.3 2500.0 17.5 145.70.66 0.32

As can be seen from the results of the OLEDs measurements in Tables 4and 5, it can be confirmed that the luminescent efficiency and life spanof the OLEDs employing the inventive compound as an emission-auxiliarylayer material were remarkably improved as compared with the OLEDsemploying Comparative Compounds 1 to 8 as the hole transport layermaterial and not forming an emission-auxiliary layer.

It can be confirmed that the OLEDs comprising an emission-auxiliarylayer has a driving voltage slightly higher than that of the OLEDs(Comparative Example 1 and Comparative Example 10) not forming anemission-auxiliary layer, but the luminescent efficiency and life spanare remarkably improved.

Further, it was confirmed that the OLEDs (Comparative Example 9 andComparative Example 18) employing Compound 8 as an emission-auxiliarylayer material showed better results than the OLEDs (ComparativeExamples 2 to 8, and Comparative Examples 11 to 17) employingComparative Compound 1 to Comparative Compound 7, and the OLEDsemploying a compound according to one embodiment of the presentinvention as an emission-auxiliary layer material showed the highestluminescent efficiency and life span, wherein a carbazole group of theCompound 8 is substituted with a N-carbazole group at positions 1 and 3of the carbazole group, and a carbazole group of the compound of thepresent invention is substituted with arylamine or a carbazole groupexcept for a N-carbazole group at positions 1 and 3 of the carbazolegroup.

It is judged that this is because a compound wherein two substituentsare substituted in one benzene ring of the carbazole group, that is, acompound substituted with an amine group or a carbazole group atpositions 1 and 3 of the carbazole group, has a higher T1 and a deeperHOMO level than Comparative Compounds 1 to 7, wherein both benzene ringsof the carbazole group of Comparative Compounds 1 to 7 are substitutedwith an amine group or a carbazole group, as a result, the electronblocking ability and the charge balance in the light emitting layer ofholes and electrons are increased to efficiently emit light in the lightemitting layer not the interface of the hole transport layer, therebymaximizing the efficiency and lifetime.

In addition, from the fact that the OLEDs employing the compound of thepresent invention have a better results than Comparative Compounds 8,wherein the Comparative Compounds is substituted with N-carbazole groupsat positions 1 and 3 of the carbazole group, it is suggested that thephysical properties of the compound and the results of elementevaluation may be significantly different depending on the type ofsubstituent group as well as the position of the substituent group inthe carbazole group.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. A compound of Formula 1:

wherein A and B are each independently Formula 1-2 or Formula 1-3, withthe proviso that the case where A and B are simultaneously Formula 1-3is excluded:

Ar¹ and Ar⁴ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si and P; a fused ring formed by a C₆-C₆₀ aromatic ring and aC₃-C₆₀ aliphatic ring; —L—N(R^(a))(R^(b)); and a combination thereof, L²and L³ are each independently selected from the group consisting of asingle bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ringformed by a C₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; and the combination thereof, R¹to R¹⁶ are each independently i) selected from the group consisting ofhydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si and P; a fused ring formed by aC₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring; a C₁-C₅₀ alkyl group;a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; —L—N(R^(a))(R^(b)); and the combination thereof,or ii) neighboring groups of R¹s to R¹⁶s may be linked to each other toform a ring together with a benzene ring to which they are bonded, andwherein R¹s to R¹⁶s not forming a ring are each the same as defined inthe above i), L′ is selected from the group consisting of a single bond;a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring formed by aC₆-C₆₀ aromatic ring and a C₃-C₆₀ aliphatic ring; and a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, R^(a) and R^(b) are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a fused ring formed by a C₆-C₆₀ aromatic ring and aC₃-C₆₀ aliphatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P, and the above aryl group, fluorenyl group, heterocyclic group,fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy group,aryloxy group, arylene group and fluorenylene group may be eachsubstituted with one or more substituents selected from the groupconsisting of deuterium; halogen; a silane group; a siloxane group; aboron group; a germanium group; a cyano group; a nitro group; a C₁-C₂₀alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted with deuterium; a fluorenyl group; a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P; a C₃-C₂₀ cycloalkyl group; aC₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group.
 2. The compoundof claim 1, wherein Formula 1 is represented by one of Formulas 6, 7,and 9 below:

wherein Ar¹ and Ar⁴, L² and L³ and R¹ to R¹⁶ are each the same asdefined in claim
 1. 3. The compound of claim 1, wherein Formula 1 is anyone of the compounds below:


4. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 1. 5. The organic electric element ofclaim 4, wherein at least one of a hole injection layer, a holetransport layer, an emission-auxiliary layer and an light emitting layerof the organic material layer comprises one kind or two or more kinds ofcompounds represented by Formula
 1. 6. The organic electric element ofclaim 4, wherein the organic electric element further including at leastone layer to improve luminous efficiency which is formed on at least oneof the sides the first and second electrodes, which is opposite to theorganic material layer.
 7. The organic electric element of claim 4,wherein the organic material layer is formed by any one of the processesof spin coating, nozzle printing, inkjet printing, slot coating, dipcoating and roll-to-roll.
 8. An electronic device comprising: a displaydevice comprising the organic electric element of claim 1; and a controlunit for driving the display device.
 9. The electronic device of claim8, wherein the organic electric element comprises at least one of anorganic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic orwhite illumination.